Update Windows test failures

What does this MR do?

Update Windows test failures

Why was this MR needed?

Add two new tests that are flaky and causing pipelines to fail when the change is unrelated.

These failures are seen in: https://gitlab.com/gitlab-org/gitlab-runner/pipelines/72607563 https://gitlab.com/gitlab-org/gitlab-runner/pipelines/72602945 https://gitlab.com/gitlab-org/gitlab-runner/pipelines/72514675 https://gitlab.com/gitlab-org/gitlab-runner/pipelines/72414229 33905821

Are there points in the code the reviewer needs to double check?

Does this MR meet the acceptance criteria?

• Documentation created/updated
• Added tests for this feature/bug
• In case of conflicts with master - branch was rebased

What are the relevant issue numbers?

Failed job: https://gitlab.com/gitlab-org/gitlab-runner/-/jobs/257107712